How to plan an epic 2025, without setting goals | Jesse Itzler

Transcript from https://podmenti.com/t/c8ddb42da8353b46

Alright, it's the end of the year, and forget New Year's resolutions, we have something much better. So in the next hour, Jesse Itzler is coming on and he has a entire process for planning.
A monster 2025. I don't want to play catch up, I want to attack.
Like now
I'm taking control and I'm dominating the year. I have other people taking it away from me. Jesse is an incredibly successful guy.
He started Zico Coconut Water, he started a private jet company, he sold to Warren Buffett, he's an Emmy Award winning rapper, got four kids, he's an ultra marathoner, he lived with David Goggins. If you don't want to learn from this guy, something's wrong with you, you're broken inside. If everybody does.
The three things that we're gonna talk about.
in twenty twenty five.
and does everything else the same. At the end of the year, if they see me in an airport, they're gonna bear hug me. I just saw Sean writing, like I
Like take notes. These are my golden nuggets from this episode. These are you know, my pen dive halfway through.
And now you added
20 winning habits. Jason Born.

They're decent boys.
Jesse's amazing. He tells us this process that he's been doing for the past 25, 30 years. I'm pretty pumped about it, and I think he will be too.
I feel like I can rule the world, I know I can be what I want to
I put my all in it like my day's all the road, let's travel. I'm glad to be back, man. I love your show.
I love that you got me back as a repeat as a repeat offender. So let me just start by saying that, you know.
I love December.
I think December and January is are critical months.
for the eleven or twelve months that follow them.
And as we head into the new year
You know, the first thing that I do
Like any business in America, when we get to the end of the year
They close out the year.
They have review sessions.
What worked, what didn't work.
You know what was successful, what wasn't successful, they give themselves a grade, etcetera.
And I found that
Um, a lot of people don't do that in their own personal lives. So I like to take a little inventory.
In December.
And just kinda have a little review process.
around how the year went and and and take inventory on my own personal year. But like
No one taught me how to
Set up my life.
You know, like no one taught me how to like
Deal with my email so no one taught me how to schedule properly.
I never like I didn't take a class in school that like, hey, you're gonna have four kids, you're gonna get bombarded
With email from
from the school with all kinds of appointments and Zoom calls that we didn't have back then and
You know, like your calendar's gonna fill up with other people's requests for your time, like
How do you want to deal with that? So you have enough time to do things that you want to do.
And achieve the goals that you want to do.
Within work and outside of work.
No one taught me that. And then layering children and layering a wife that works and a business as an entrepreneur
And like
How do you do that?
So you know, like
I'm a product of trial and error. I tried a lot of stuff.
I didn't grow up with a phone. I was scheduling everything on a paper calendar.
For
Literally forty five years of my life.
Um you know.
And um
And I had to figure out like what
as my life evolved, how to grow with it.
So I have a pretty cool system. I'm happy to share it with you guys. It's worked really well. It's allowed me to
to balance a lot of things and get a lot of things done. And I think it's pretty simple.
And I I will preface it by saying that
Um, you know, as you get older.
How old are you guys?
Thirty five and thirty six, right? Yeah, thirty six.
All right, so you got another maybe decade.
before this hits, but it will hit.
And it's inevitable.
As you get older
Creating newness.
becomes really hard.
Because you live in routine.
You know, and like it gets very comfortable.
to be to live in routine. And really I found that the only way to really
guarantee that you create newness. And newness is important.
It's important to relationships.
It's important to your momentum.
And your enthusiasm.
An your success.
And your excitement towards things and your growth.
The only way to create create newness I found
Is the planet.
And or leave room to be spontaneous.
So I become a really aggressive planner.
And I feel like a lot of us play
Um wife on defense.
Our calendars fill up with other people's requests for time, like I mentioned, Zoom calls weddings, appointments, school stuff.
And at the end of the year, like you don't have a lot to show for it.
What are the categories? I do family fitness finance fun. Do you have like your own like cute acronym f uh
For your categories.
Well, I do my own individual personal audits for business with my teams.
But then from my personal thing, adventure is a category for me.
I try to look through like what kind of adventures did I have.
Well, like I said, and we'll get into this in a minute.
You know, you wanna have something to show for all your hard work at the end of the year, not your Zoom calls.
I'm not like yes in October. I lit it up on Zoom.
I'm not doing that. I'm like, oh, I just I just took a one on one trip with my daughter to New York City. I just got back.
So stuff like that. I'm like really taking inventory on
How much time did I spend with my kids?
You know, like what did I do well? What I do what I have to work on in my role. Like I really, really do do that.
And then I try to close out the year.
And I have a system
for closing out the year. I'll share with you guys really quickly. The the first thing that I want to do is
And like the overall theme of closing out a year, and I think everyone should take
A couple of hours to do this.
I think it builds momentum.
And I think it gives you a little closure around the year, whether you had a great year or a bad year.
It gives you a fresh start.
for twenty twenty five, which I think is is really, really important.
And um the theme is I wanna come into the new year light.
I want to feel light and I want to get rid of
All the email baggage.
All the to do lists.
All this, I don't want to have a lot of carryover going into the new year. I want to kind of clean my hands and just be light. Now, this might sound ridiculous.
It starts in my closet.
I go through my closet, I look at all the stuff that's been hanging there.
for twelve months that I've never worn, you know.
And I donate it.
I get a big bag.
If it if anything is a fifty fifty, do I want to keep it or don't want to keep it?
I just say someone needs this more than me. It goes in the donate box.
And I start to organize my closet so when I walk in
I don't have a ton of decisions.
You might see me wearing very a shirt.
Very similar to this because
I don't have a lot of options.
You know, I keep what I like, I get rid of what I don't like.
And I get super clean my desk.
I get rid of all the clutter on my desk.
I wanna I don't wanna walk in and I got stacks of things I gotta go through and bills and stuff.
I get super clean on my desk. My emails.
I'm a big hit delete and explode'em all at the end of the year, guy.
Um but before I do that, I put things in files. I respond to the things that I owe an answer to.
I delete the stuff that I don't need. Everything else goes into a folder.
And I try to go in net zero.
into twenty twenty five. That's really important. I don't wanna
Come back from our vacation January one.
and be sitting with an inbox with seven hundred emails and just like
You know, just feel like I had to play catch up.
the first thirty days of the year. I don't want to play catch up. I want to attack.
I want to attack.
So I come in I come in naked on my emails.
I unsubscribe.
I go through all the stuff that I have subscriptions to.
I unsubscribe.
I un I delete all the apps that I think use again.
Just trying to get light.
You know, I get rid of all clear out all the apps. I clear out my cars.
Make sure that you know I have no clutter in there.
And um I create files for twenty twenty five.
Where you know, maybe I I'm still a paper guy, so I keep
records of my
Medical files. I know people have them on digitally, but I keep a paper file. I still
Yeah, my bills.
Paper.
I put'em in files, so but again, I I have a system.
So I'm not like playing catch up.
And um
So I call I get super light on all that stuff.
And then
I can't recommend this enough.
I write handwritten letters.
To
But
twenty to thirty people that really impacted me or helped me.
Even you guys, man, having me on. You know, you might get a thank you no. Thank there's eight billion people in the world.
Guys.
Thank you too for having me on your podcast. Like you thought in me.
Thank you.
Alright, I
And you know, a handwritten letter.
to my suppliers, my contractors.
Maybe a teacher, my son's coaches for football. I want to thank them this year.
You know, um
With no purpose other than really giving like a thank you.
I've been doing this but that for thirty years.
When I was twenty three years old.
And I had no money and I was sleeping on
eighteen different couches. My entire marketing strategy was I wrote ten handwritten letters a day.
And I mailed three thousand letters.
I'm not even kidding.
And I still to this day do that because it breaks through the clutter.
People remember it.
People leave their mail. They might not read their
DMs, Tex, Slacks, and all that stuff, but they read their letters.
They come in the mail.
And there's a different intention.
I took the time, I wrote it, I linked
The envelope, I went to the mailbox, I put a stamp on it, I put it in there like
It comes with a lot of love, man.
It's a lot different than hitting send on an email. Are you still doing all are you still doing all that, or Sam, I'm not gonna talk about anything I don't do. No, what I meant is uh
I've like wanted to send email uh letters to a lot of people and then
I'll be like
Is there a service where I can just type it out and they mail it out for me?
Yeah.
Doesn't work that way.


He's like, Are you listening?

No, I I the audio coming through. I do it by the way, I send letters as well, but then up like have a stack I have like um
A few years ago I got some stationary and it like it feels good to like write letters to people. But every once in a while I'm like, I don't feel like writing this.
Is there a service? And then I'm like, What the hell am I doing?
And so I wasn't sure what you were doing.
Yeah.
You can't outsource it.
It can't outsource it, you know. Um
As a business owner
Like
I've realized that it can't outsource soul.
You know, and the DNA of a business
And is the soul of the business, the heartbeat of a business.
You can't outsource that.
And customers feel so.
And your friends feel soul.
And when you start outsourcing things that
You know, for hundreds of years humans have been doing themselves
It loses a little bit. And I found that that two hour investment
How about this? Let's do an experiment for your listeners.
Take ten envelopes.
Ten take ten pieces of paper.
And take twenty minutes.
And right.
A thank you note or to your parents.
To your kids, teachers, whoever.
Say hey this year
I just wanna thank you for investing so much time with my kids or whatever you want to write.
Lick the stamp.
Put in an envelope.
And watch the return on investment.
Watch the return on investment.
And I found that
Um there's nothing like quite like it.
Now that might sound ridiculous, hokey.
But I've been doing it for thirty years and people still thank me.
No one gets a letter.
From you.
like that and doesn't remember or hit you back.
Uh, there was a guy who came on, by the way, and he held up he was he does the same thing.
Uh, this guy Guy Speer, he's value investor, and he held up
He goes, I do this, but he's like, Why did I start?
Because I went to um the Berkshire Hathaway summit.
And I went to this event and then he goes afterwards, here's what I got in the mail. And it was a letter. Warren Buffett had written him a letter. And it was two seconds. It was
Guy
Thank you for coming. Really appreciate you being there.
Sign Warren.
And he goes, If Warren Buffett is doing this, I can do this too.
I get one from Coach K. I know you're a Duke guy. I get one from Coach K every year. Check this out. Look at this.
Show you guys.
Yes.
All of these letters.

All of these letters and there's
I have
Boxes of these. All of these letters. Check this out. These are all letters.
That I got this year.
I've read'em all.
I keep em all.
In this box.
And at the end of the year, it's going in a thing, and then I'm starting a new box that's gonna say twenty twenty five.
Because I've been talking about this.
For a long time.
And um
You know, I'm in a really unique spot. I'm in a business where people write me letters.
You want to talk about
Finding your mission.
Imagine

Waking up, going to your mailbox.
And and and to to letters of people thanking you for
you know, sharing best practices or
You know.
Helping whatever it is.
What a what a gift.
What a freaking gift.

If if everybody does
The three things that we're gonna talk about
In the next twenty minutes.
in twenty twenty five.
And does everything else the same.
that they did in twenty twenty four. At the end of the year, if they see me in an airport, they're gonna bear hug me.
'Cause they're gonna be like that was so easy.
And I can't believe how much better.
My life just got.
That's what we're gonna cover. So the first thing is is closing out the year.
Getting light.
Doing all those things.
You know, to get light, writing handwritten letters.
And then the the other thing that I do is
I I try to identify like
What I wanna
Fix.
going into next year. Because
You know, like everybody wants to be a ten out of ten. No one signed up to be an eight out of ten, the eighty you know, a B minus.
Everybody wants to be as close to the a ten at a ten.
But if you have certain things that are broken
Even if you make a bazillion dollars and your business goes up fifty percent and

You're never gonna be a ten out of ten if like
The marriage is broken.
You know
Something's wrong.
Whatever.
So what I always tell people to do is
Imagine you guys had it, you guys can do this right now.
Imagine uh you had a big blender.
And in the blender.
You put all the buckets, Sam, that you were just talking about, all the buckets in your life into the blender. Your finances, your health, your weight.
Your relationships, where you live, like
Everything going on in your life, put it in a blender, shake it out.
And then on a one to ten.
With ten being like the ultimate in happiness.
And one being rock bottom.
Like
Again.
What's your number? Your weight, your relationships, your work, your finances. You put it all in, you shake it out. You're seven.
Are you a five? You'll have to tell me.
Are you an eight? Are you well like what are you?
Now what I love about that exercise is
Immediately your brain goes to a ten.
And then the two or three things that are bothering you pop in your head like crystal clear.
And take that number down.
So maybe it was like, Oh, my finances aren't there or like
I hate my job or
Things aren't great in my whatever came into your head.
Those are the things you gotta work on.
They're not gonna magically get better.
Hey.
You don't just like
Oh.
Yeah, like
My my relationship stinks. It doesn't like magically get better.
You gotta work on it.
And did anything pop into your guys' dead?
Right away?
Yeah.
I I put it all in the blender.
I got to an eight and a half and right away you're you're right. I started at a ten,'cause I'm s I'm happy, right?
And I said, Well
I do
The weight's gotta come down a little bit. All right. The weight's gotta come down a little bit. So that's a that's a point off, you're not
I wanna have healthy habits that I'm proud of.
And then the second one was
Um
You know, I
I think I'm really good at this content thing. I love making content.
But I'm still spending way too much of my time in my businesses.
And I I really want to make that shift from operator to creator. And I've made I've made I've made good progress, but I'm not all the way where I want to be there.
I had a six. I had a daughter and I'm loving being a father and she's fantastic. That's a ten.
Finances. I did really well.
That's a ten.
But I'm bombarded with inbound messages and I don't have uh a system to where
I'm saying no to ten minutes at a time.
Uh the ten minute
Time requests and
context switching is m ruining my life and it feels like I can't get in the flow. So I'm gonna give my give it a six.
Okay.
A six overall.
Yeah, because the
Context switching, it like
I get m so much joy.
being in the flow of something and uh both a combination of lack of system and
addiction to social media and text and all that shit.
It's brought me down a a a whole bunch.
You know, two thoughts. One, when you're doing the exercise, there's no comparison against anybody else.
So like you know, if you are comfortable with the money you're making or whatever, you're not comparing yourself to Buffett.
It's like
You know, I'm comfortable where I am. You're never gonna win the comparison game.
'Cause there's always gonna be someone.
So that's one thing just to think about.
And then you know, not to knock you at all, Sam. I think I was super honest of you.
But like for anybody out there that was a six, if like if Mike's
Son comes home with a sixty on a test, it's an F.
Yeah. No, but I'm agreeing with you. Like it it it brought me down a lot.
But the good thing is it's all fixable and you have to identify it and like
Look, I'm not here to be a therapist or preach. All I'm saying is
knowing what those things that are that need a little bit of
Help and if it's your weight.
You know, then just in twenty twenty five be like, you know what, man?
Everything's clicking.
I'm gonna address this.
I'm just gonna be a little that's all.
You know, so
Yeah, but you have to identify
My point is for the listeners
Like
You gotta identify it because
If you don't it just keeps
Compounding.
And and then you're playing it's just harder to like
Catch up when it's compounding.
So you close out the year, you get light, you clean the closet, clean the desks, clean the cars, you c
d email bankruptcy, you get the files, you write the handwritten letters, you give thanks.
You do the blender exercise, you identify the two or three shifts I'm trying to make.
That's is that cl is that how you close out the year or is there anything else to that?
And just to make it super practical, are you like writing this down? Are you just thinking about it? Do you say it out loud? Do you do this with somebody else? Do you look at your calendar? How do you even go back through the year? Can you just give us like
If I wanted to sit down an hour after this,'cause I'm so pumped after this episode, I wanted to go do this.
Can you just give me the like kind of the a little more detailed instruction on how I would do it?
What
I get really excited about getting light. Like, you know, so I don't have to write anything down to clean out to clean my closet and my desk and my emails. Like that's all just something that like
You know, you feel accomplished.
When you do that.
And
We're doing all the other stuff anyway. We're we're we have businesses, we're doing all this, but
You just feel really good about yourself.
As far as like handwritten letters, I do make a list. I keep it every year of like kinda just
Man, I just think about like what podcast were I on for me.
was I on who really went above and beyond for me this year.
or my kids and my family.
You know, I had a I went on a trip to to Africa. We had a great tour guide.
Um, I had a gentleman in Kenya that ran with me every day to to like chaperone me through the jungle.
I'm gonna send him and like just that kind of stuff.
And I don't want anything for it.
Just makes me feel good.
And I know probably makes them feel good.
So I do all that.
And then I and then like again.
You just took that exercise took
Thirty seconds to identify.
What we gotta work on.
And then I just make a mental a mental note about it, like, you know, I want to get better at it.
This whole process we're talking about like
Super fast.
All right, so that's the first thing.
The second thing I do is I have a planning system.
That I've been using.
that I I swear by it's there's three steps. And this is what I was talking about. If you do these three things
You're gonna bear hug me.
Very simple.
So the first thing that I do is
Um, there's an old Japanese ritual.
Called a masogee.
And we took we took the liberty to tweak the exact definition of it. It but but
The way we look at it is that the
The concept around a misogee is
Every year.
You do one big year defining
Right.
So again
At the end of the the year, even though you're busy with all this stuff, you have one year defining thing.
That to really show for
your time over the three hundred sixty five days. So for example, like
Two years ago, and this is big.
I rode my bike across America.
Last year I did rim to rim to rim.
with some friends. In twenty fifteen I launched a book.
Living with the seal twenty seventeen.
I launched a company called Twenty Nine O Twenty Nine. Like
Every year going back literally to like
You know
Twenty years ago.
I can name like the one thing that I did.
That was really, really year defining. So at the beginning of the year
I just I might not have that idea and that could be like I'm gonna launch a podcast.
I'm gonna quit smoking. I'm gonna run my first marathon.
You know, but like
What is that one thing that you're gonna look back to someone says that I was unbelievable, man.
I rode my friggin' bike across the country.
I ran the New York marathon this year.
You know?
I think that's really, really important. Now A
It's important because
Like you wanna have something to show for it, but B
Um
I find when you have something on the calendar.
a goal, something like that you're something that you're working towards.
Um
That's challenging.
You you show up.
At work and at home.
completely
Different.
You show up completely different.
A
If I'm running the New York Marathon
Sam, I now have to say no to the things that that
I don't have the time to get people'cause I got a train.
I'm adding you know hours of training in. So now you have a vehicle to say no to things.
But B is you know, if something that you're looking forward to.
one of the books that I read this last year, I think it was Michael something uh Easter maybe, uh The Comfort Crisis and he talked about the Masogee. I had one. It was a fifty mile race and the the the Masogee was uh you have a fifty percent chance of failing. Uh I ended up uh uh
hurting my Achilles really badly and I was like, Fuck. So I I failed.
Uh
And it was awesome though. I look forward to I'm picking a new one now.
Um
Yeah, but you
You didn't fail, Sam. You just didn't finish. Yeah, yeah, yeah, yeah. It but but it was hard ass work and it was awesome. It felt great to have that on the calendar.
Yeah.
But what you did
Was amazing.
You're saying I'm gonna go double the longest run I've ever done in my life.
Okay.
I'm gonna do an ultra marathon.
On top of everything I I have going on, I'm gonna challenge myself. It may or may not work.
That that's not an F.
I mean that's an A in adventure.
You just didn't finish it. I mean
Not everything we do is gonna work. I've had businesses that have failed, races that I have DNF.
But I love that you put it on your calendar.
Well
My kids.
I have four kids.
Fifteen, ten, ten, and nine.
All right.
You know what they're talking about right now?
They're talking about that we're going skiing.
In two weeks.
So
They're going to school and I'm like, guys.
Two more weeks of school, then we're going ski.
Because that's on their calendar.
It's helping them.
go through school focused lock in because they know they're gonna get this reward.
Winter vacation.
Coming up. Adults are the same way.
Like I'm willing to go work really hard if I know I have a vacation coming up.
Or a race that I'm gonna do, or something that I'm excited about.
So having one big year defining thing
Really important. Do you know what yours is gonna be for twenty five?
I don't.
I don't, and that's okay, but I know that I'm gonna have one.
And what it does is it also like opens up my mind to adventure.
Wh which Masogi do you look back out on most fondly?
Uh if you look back, you know, ten years or so.
I did a race called
Ultraman.
Which is a six point two mile open water swam.
A two hundred and seventy five mile bike and a fifty two mile run.
And
I
I I was insanely
I was going to defer to the following year, two weeks before the race.
Because
I didn't s I didn't swam at all.
I
I didn't I didn't have a wet suit.
And the water was fifty seven degrees. So I called it my friend who's a coach and I'm like
You know listen.
I haven't been training at all.
Zero.
And there's no I don't think I can do this.
And I'm thinking about the Fering, thinking he's gonna be like, Of course.
Defer train so you don't get hurt.
And he was like, absolutely not.
The challenge is gonna be you know if you train for a year, you're gonna be able to do it.
You have no idea if you're gonna do it.
Dude, a six a six mile swim?
Alone would take like three and a half hours, right?
Or if you're a bad swimmer like me, five.
But yeah and also like fifty seven degree water is is
I I did a mar uh a marathon in fifty seven degree. It was horrible.
Or triathon. It was awful.
Sam.
I showed up to the event and I jumped into the water the day before.
And my f I
I've literally like my face hit the water.
And it was like You're like I'm out.
Ow. I'm done. It's like it's like it's like getting punched in the nose like with the first time when you want a box. You're like, this sucks, dude. I don't I don't want to do this.
But I finished it. I finished it.
And um
You know
When I was going through this event
Those th those kind of challenges, it's really important to break things into digestible bites.
If you're starting a business, you want to put things into digestible bites.
So when I started Marquee Jet, if they would have said
You need
FAA approval, department of transportation approval, build the sales team, raise my I'm like a kitty pool attended for you. What are you talking about? I didn't what would you say the first thing I needed was FAA approval?
Well there's gotta be a lawyer that does that, specializes in that. Let me get
Got that guy, got what was the second thing we needed? Like
So it's the same thing here.
I got a swim temp six miles, impossible.
Can I swim to that
To the next bu to the buoy?
Yes.
Can I swim buoy to buoy?
Yes, so let me just break this down.
into forty buoy to buoy swins.'Cause I can
Let me break the I can run for seven minutes.
Forever.
So let me run for seven minutes, walk for three.
And just repeat that cycle.
And that that's sort of how I attacked it.
In any event.
We pick him as Soggy.
Right. So I don't know what mine is yet, Sean for next year.
But I know I'm gonna have one.
And just
For the listeners.
You know, just the notion of like, Yeah, you know what?
I wanna have something
On my calendar.
Now you're like
You've like reprogrammed your brain to just be aware of adventure.
And that's already a step in the right direction if you're head down in work.
The second thing I do is
Something that I've named after my friend Kevin. I call it Kevin's rule.
Kevin and I were took our our children
His daughter and my son.
My son was eight at the time, I think his daughter was nine.
to Mount Washington in the winter.
It was
It was like minus thirty with the windshell.
And we've a minus forty sleeping bag. We're sleeping in the snow.
It insane.
And we're camping out overnight and I'm like
Kevin
Is a police officer in New York, I'm like
There's eight billion people in the world.
We're the only four people.
In the middle of Mount Washington, man.
This is amazing. I'm like
You know, how often do you do stuff like this?
And he lights up, he's like oh
He's like every other month.
I do something one day or one weekend.
That I normally wouldn't have done.
I'm like, what are you talking about?
He's like instead of like watching the Georgia football game
I'll take my kids fishing.
I'll come to Matwine I've go visit my college friends.
Oh my
Well why?
He goes, Well
If I can't take one day
Every eight weeks.
To do something like my work life is
Is that is out of balance, but
If I do that
I'll have six little mini adventures a year.
I'm like, yeah.
He's like well how how how old are you? Well, if you're thirty five
Sean, you live to be. Let's say you live to be.
Eighty five.
That's fifty years.
If you do those two things I just said.
You have.
Fifty.
You're defining things.
And three hundred
Mini adventures.
That's an insane life.
Well that's an insane
Life.
At the end of the day, by a
Fifty Ultraman kind of things.
And three hundred mini adventures?
Just because I managed my clock right?
Like I won life.
Do you're
mini adventures and your Masodi? Like do they stack to where it's like
Well, I already did the Ultraman.
What's like the ultra ultra man like are you trying to one up'em each time?
Not at all.
I'm just looking for things that
That excite me.
Um
So this actually this year I do have
A
It it's not challenging enough.
For me to consider it like a Masoge.
But I'm going on it.
A a tour of the world's best saunas in Finland with twelve friends.
So we're going for ten days, we're hitting thirty
Thirty plus saunas.
Over the course of twelve days.
In s in Finland.
And
You know, so that is my
A big thing or
For twenty twenty five.
Hey, real quick, if you're liking this episode with Jesse, you gotta listen to the first one we did with him. It's the story of how he built his fortune, his first business, how he failed, and then ultimately a mentor stepped in and gave him some some tough love, let's say, and turned his life around.
Uh, he tells a story about how he started a private jet company, ended up selling that to Warren Buffett. There's a Matt Damon cameo in it.
Crazy stories from this guy.
He also brainstormed business ideas of what he would do
If he was young and needed to build a fortune from scratch again. So go check that out. It's episode number five oh four. You can either Google it or in the show notes below. We're gonna put a link to it. And also.
At the end of this episode, we are giving away a few thousand dollars of his
big ass calendar, the one that he uses to plan his twenty twenty five.
We say the code at the end of this episode. So listen to that and then you can go and get one of those for free. All right, back to the episode.
So if I'm getting this right, the Masogee is more of
A challenge.
Something that excites you, something that f it's a big adventure. It's year defining.
And you have the
You'll get the fun of progress along the way as you make progress, you'll get the anticipation, and then you'll get the year defining a sense of accomplishment. Whether you win or just
You did it. Um
And then the adventures are more about
Is that just more about non routine?
So just kind of making sure you are not just every Saturday we go here, every Sunday we do this with my kids and just shaking up the routine with something fun. It doesn't have to be super challenging, but is that the right way to think about those?
Absolutely. It's it's non routine, it's planning adventure, planning newness.
It's prioritizing yourself.
And it's not l it's it's playing life on offense. It's not letting your calendar fill up
You know, look, if we just sit back
It's gonna be weddings.
Meetings.
Conferences.
Appointment.
And the fake.
What do we do? What are we doing?
How many of those things are uh Jesse and by himself or with buddies or just like the family?
Um
I love to
I love to do things with
with m my friends and I love to do things with my family. I treat my family stuff
Differently.
So I also plan family trips, but you know
Um I have the luxury of time.
You know, people talk about rich.
And and the first thing that comes into your head is like money, obviously. And that is important. And clearly that's an important part of being rich.
But
There are so many buckets of rich.
Are you spiritually rich?
Are you time rich?
I'm insanely time rich.
Right now.
Which I think is the most important thing, especially in your fifties.
I'm insanely time rich.
So I can
I have the luxury.
Of
Doing things spontaneously.
When I want, et cetera.
I'm spiritually rich. I'm socially rich.
If we did a little sidebar here because the three of us
are all lucky to be in a position where
We don't have to work. We could all we could just spend all year training for a you know, an MMA fight, an amateur MA fight or whatever it is. But I think a lot of people who listen to that, you know, may not be at that.
Yeah, they still have the job, they still have w whatever the the you know, the day to day responsibilities. So could you take, you know, thirty seconds to sort of speak to like how you would
May uh is there any difference in how you would approach it, you know, the bestotis of the adventures if somebody's not like
Yeah, financially free where their their calendar is theirs to do whatever they want with. Listen, I have been doing this.
Since
My journey was insane.
It was crazy.
My twenties was were spent on couches.
Friends, apartments.
You know, um
Just trying to like figure it out, pay my rent.
You know, all that stuff.
But I was still so rich with adventure.
Every year I would go to the Coney Island Polar Plunge.
On New Year's. In order to cost?
Subway token.
You know what it cost to do the trip to Mount Washington with my kids?
eighteen dollars to part.
We live in a country.
At offers
The most insane rivers
Mountains.
National parks.
Oceans.
Hikes.
Drings.
I mean
Conferences. Like
Okay.
You can fill up your life with adventure.
I should write a book.
Filling up your life on adventure.
You know, for under four hundred dollars a year. Because you can do it.
Now so you know, I I I understand that obviously my can be bigger and it's easier for me, and that's true.
But
You know, I've been doing these things for
For a long time. I just took my son.
To the polar plunge at Lake Lanier here in Georgia.
Um you know.
Um
Th there's just so much stuff that you could do that again is outside of the norm.
You know, people think like you don't have to climb.
Mount Everest.
to feel like you've accomplished something.
You have to just get out there and do something that makes you proud of you.
You know?
There's a there's a great story.
Uh you do you know Burn Brene Brown?
So she she has this great story she tells about like her daughter
going to like a swim beat and she was scared to do like the swim
swim beat. She was like, I'm not gonna do well. I'm you know, I'm scared I'm scared even to swim, blah, blah, blah.
And she she talks about how, you know, her daughter
After the swim meet, you know, she lost the race. She maybe got licking it, whatever. She wasn't didn't do so well. She got out. She was feeling kind of bummed.
And Brene Brown's quote is like
You know.
Winning isn't a winning isn't always about getting first place. Sometimes winning is just getting off the block and getting wet.
And uh like you know, you jumped off the blocks and you got wet, like
That's a huge win. You you you have become a more brave person by having done that. And I think there's
Uh there's something to that. Cause you know, when I hear about the ultra marrow uh ultraman races and stuff like that, I'm like ah
Yeah, that's a so far from where I am.
But at the same time, when I heard this Brene Brown quote about sometimes winning is just getting off the block and getting wet, that changed my perspective. I started doing a lot more stuff because I changed what winning meant.
Also, Sean, I like I think a lot of people listen to this stuff and they're like, Oh, Jesse's into fitness shit and you know, I'm also into uh I like weightlifting and things like that. And I think they like say like
Well, I need to go and do a marathon or a long race.
That's not true. I think that you can do
things that fit your interests significantly more because like he's got a hat that says all day running, running your passion. Like I don't think you have to necessarily do something that falls into that endurance category or whatever is popular.
I wanna this year, Sam, I wanna go to one of those silent retreats where you sit
In a dark room for two or three days.
But listen.
We're going into a new year.
All right.
And I'm giving suggestions and I recognize that everyone is
In a different
Has a different dynamic.
Time is different, finances are different.
But
I what what I'd love to get out of this call is I just want to fire people up.
For the opportunity that we all had.
to have an incredible twenty twenty five.
You know, go master something. Go learn a language.
You know?
Go learn a certain skill.
Go volunteer.
You know, do something that makes you proud of yourself at the end of twenty twenty five.
That do something that makes you feel accomplished and proud of yourself.
I'm twenty twenty five. Now
I'm not saying go ride your bike across America.
Just cause I did that? No, not at all. But do something.
that you look back on the year and be like,
This was this was amazing.
You know, and I'm just saying that there's a lot of things that don't cost money.
If you're intentional.
If you schedule it.
Which we'll get to in a second.
And you play a little bit of offense.
So Masoji, Kevin's rule. The third thing that I do is very simple.
Yeah.
I found this works a lot better for me than New Year's resolutions and
Maybe maybe.
Different for other people.
But rather than doing all these goals and stuff, which I like never accomplish
Um I very simply every quarter.
I add a winning habit.
to my life. For so for example, like I I don't drink enough water.
I'm gonna drink a hundred ounces of water.
You know, um
as a new habit. I'm never gonna be late to a meeting. I'm gonna add a 10 minute a day meditation practice.
You know, I I I don't know, but like last quarter.
This is crazy, but like I'm so inflexible.
And I found uh something on YouTube that was like physically inflexible. You're like, I can't even touch my knees.
You know, so I found something that's like
Five exercises you should do before you have a cup of coffee. Like first thing you do when you wake up. So I've been doing these five stretches. It takes six minutes.
Pretty much every day.
And um I can send you guys the link. They're really easy. So that but but my point is
We we are
A product of winning habits.
Winning routines and a winning mindset.
That's what we all want. We want to have winning routines.
Winning habits.
And a winning mindset.
And
By layering in. Imagine if you do that.
Let's let's just say we took a five year look on life.
My life's gonna radically change in five years.
I have a fifteen year old son, he'll be a college.
My my kit my little boys now.

In high school, like
I like to look at things in five year windows because
Like if your parents are in it are are elderly
They might not be here in five years. Like mine mine were five years ago.
Mine aren't now.
Like your life
Changes
Friggin' like this.
Gotta think about this stuff.
And imagine in five years, you just did the three things that I said.
You had five insane
Experiences.
You added thirty.
Many adventures that you went and had.
by taking a you know six days of three hundred and sixty five a year.
I mean, come on, man.
And now you added
You know, you added twenty winning habits.
You're fucking Jason Bourne.

They're decent board.
And like this is not difficult.
Well, so uh all this stuff I'm like
This is badass. Okay.
Tell me how you plan it and how you actually put it in practice. You're saying like
You're a s you're a product of your habits and things like that. What's the habit of planning and like thinking of these things and actually getting them on the calendar or whatever?
So I don't know, you know, people listening to this audio or video, but this is my entire twenty twenty five.
If you're not on YouTube, he's holding up the big ass calendar.
So
So
I
As soon as I know I have something I
For me.
I put it on my on my calendar on paper. I write it down. Now there's a lot of research around writing it down versus putting it in your phone.
Goals that are written down versus
You know, there's a ton of research around that.
But as soon as I have any of these trips
I put it down.
I put all my big events for the year down immediately, last day of school.
First day of school. If you have kids, first day of camp, if they go to camp, last day of camp
Famp spring break chips.
Date nights with my wife.
Every um I take a quarterly
Um
staycation or trip with my wife.
My wife and I have our own little system.
We have a date night once a week, Wednesdays.
And then every quarter
We try to plan something together.
Could be it like we're going to New York next week.
But it could be just we're gonna have a an overnight staycation here, but
We try to make sure we have
Four year old.
Date nights as much as we can.
Family dinners.
And then the rest is just family trips.
Dude, you travel a lot.
I travel a lot, but I put it on my calendar.
Because once it's in my calendar, now I have permission to say now.
Uh, I wish I could go to dinner with you guys, but I'm actually
Um
I'm camping out with my kids that weekend.
Like now.
I'm taking control and I'm dominating.
The year.
Not other people.
Taking it away from me.
Oh, you can laugh about it, but I'm dead serious.
I'm not sure. I think it's cool.
You know that experiment where they take a jar?
And they're like, All right, you have these rocks and these sand. Fill put'em the put as much as you can in the jar.
And basically if you put the sand in first, you can't put any of the rocks in, right? Because all the little meetings and appointments and zoom calls and everything else.
Takes up all the space versus if you put the rocks in first.
And then you could pour as much sand will fit all the way around it. That's basically kind of like the
the model of what you're doing. You're basic saying
I'm gonna put all the shit I really wanna be intentional about, the life experiences I'm gonna remember with the people I care about. I'm gonna put those on the calendar first, and then I'll let all the little knickknack appointments.
fill in around that where there's still space. And if I do it the other way, like most people do
What you say?
Yeah. Yeah, like when I have time, then I'm gonna do something great. And then they never have time and nothing ever happens. The rocks never get in.
Exactly. And the reason why, guys, I like to have this on one big visual
Like
Look at all three hundred and sixty five days on one page.
The reason why I like to do that is A, I'm visual.
Like I need to see it. You know, we're all we all kind of think in pictures and we think visually.
But now two two things. One
I can see where my gaps are.
I can see where my gaps are where I have
More time available and not.
Two.
I can track towards my goals so much better.
Then versus like if they live, you know
in my phone and I use my phone for my appointments, Zoom calls.
And all that stuff.
But I don't like scrolling through it to be like Oh, my marathon and I'm scrolling all the way to November.
I like to see it like oh I've this many days.
It's like the road map is visual.
So for you know
To have it all on one big calendar.
Is is really helpful.
And I'm super spontaneous.
You know, I know that
Look.
If you don't plan it, it probably won't happen.
So knowing that a after being on Earth for
Five and a half decades.
What do I do? I want to plan as much as I can. I want to get in front of it.
So I sit with my wife
We sync up all of our stuff.
You know, in twenty twenty five we're going to I'm like I said, I'm going to Finland.
We have a trip to Japan.
We're going to Greece.
You know, we we have put all this down on our
My twenty twenty five is already mapped out and it's insane.
All I have to do is follow the script.
Now
Yours might not be as
As you know.
Wild is mine.
Um but
The point is you control it.
And you can map out this incredible year.
Do you but do are you picking those quarterly habits as well as those mini adventures? I'm not.
I'm not because I'm open, I'm I'm always listening to people and
And
When I was when I had Marquis Jet, which is a company that I had
I started with my partner when I was I don't know, twenty nine, thirty years old.
Um
My dad owned the plumbing supply house.
I had no relationship with money.
We never talked about it.
I had no business experience.
I didn't know shit.
And
All of a sudden I had this
Private Jack Company.
We're flying.
Three thousand of the who's who of pop culture.
CEOs, top CEOs, athletes.
Entertainers.
And I'm getting access to these
People.
And I'm really curious. I'm thirty years old.
And any time I had a minute.
with anybody at the airport. If I was visiting a customer client.
I would say to them like
I wanna know how they ri lived rich.
Like you mentioned, people here might not be
Well they might be one day.
Who's gonna tell them how to do?
Where do you vacation? What do you do with your money?
What time do you go to bed? How many newspapers do you read?
I want to know it all.
I wanna know the best habits.
And routines and mindset.
From the best people.
On the planet.
I became a sponge.
And I remember asking this guy, sitting down with this guy.
I'm not gonna say his first name is James, he was insanely wealthy. I'm
thirty. I'm like nothing.
And I I asked him, I said, James, how do you live rich?
And he's like he said to me, I read and you walk me through his through his day and
where he vacations and what he does with his money and how much gold he has buried in his back yard and all this shit.
Never forgot it.
One thing that he said to me.
One thing he said to me.
He goes, and I take three hours a day for myself.
And I'm like, I can never do that. Well no, it's cumulative.
I'm like, well what does that look like for you, James?
So I might take up.
thirty minutes on in the morning. I might take a little time at lunch to read, go for a walk.
Work out.
Da da da da. The end of the day it's about three hours a day for myself.
And
I I I was like since then I'm like
And I was like, why?
And he was like, Well
You know, if you check the U box
You show up
As a parent, husband, CEO, boss, employee.
So much better.
You don't resent your wife or your husband or your partner for taking away time.
Are the things you want to do?
All this stuff, long story short.
I started taking
Two or three hours a day.
Right after that meam if they worked for him.
I'm not gonna wait till I have a bazillion dollars. I'm gonna do it now.
So time rich.
Something that we talked about earlier.
Does it mean you have to be rich to be time rich.
You have to be organized, scheduled, and allocated.
To prioritize you.
And that's all I'm saying for twenty twenty five.
You might say, Jesse
This is hokey pokey fine.
But all I'm telling you is
Carve out time.
For you to give you adventure.
Make you feel a cop work's always gonna be there.
It's always gonna be there.
On a week to week basis, do do do make a list of your to dos.
For the week before.
Yeah.
So
Um
I look at my week
On Sunday night.
I take it.
from my calendar and from my phone and I put it on
Paper. I use a planner.
But you can also just write a piece of paper and I write down my day. It's like
I can move things around and then I can prepare better. I know it's
I like to have a week at a glance.
View of everything.
And then and then the last thing I would say
This is less like a little
Bonus thought for people.
Is remember when you were a kid and I don't know if your parents gave you vitamins.
Did they give you vitamins when you were a kid? Like for school. Flintstones, vitamins, for sure. Yeah, Flintstones, right?
I had Flintstones vitamins as a kid.
Yeah, like
anti Flintstone vitamins, but that's that's that'll be podcast number three.
The the
The the vitamins were like
You know, you take one vitamin
And it had like
Yo five hundred percent of everything you needed in every category in like one little pill.
And that's unbelievable, but yeah, you took your daily vitamins and it checked all the boxes.
So I have my own version of this that I do Sam.
Um and Sean. That works really well.
So I
If you made a list
Imagine you're all the time in the world, you could do whatever you wanted to do every day.
Well, how would you spend your day?
Well I know exactly what I would want to do. I love saunas. I love coal plunges. I love running.
Biking, swimming, and exercise.
I love doing breath work. I love taking walks with my wife. I love playing with my kids. Like a very clear.
On what it is by the way, no when I say up do I say
I love buying art.
But I don't those are the things I love to do.
A very simple.
I inherited that from a very simple man, my dad.
V
Let's say I have ten of those things on my list.
Okay.
Those are my vitamins. Those are the things that make me strong.
That I need.
Every day.
I try to do two or take two or three of those vitamins.
I can't do'em all.
But
I I try to do two or three. So today
It's we're recording this now, it's one o'clock.
But I've already gone for an hour run.
And I've taken an hour sauna.
So of the three hours I allocate for myself.
I've already done about two of them, so like my day's good.
And I've taken two of my vitamins.
So now when I show up for you guys.
I'm all in. I'm not outsourcing.
Like we talked about, I'm all in.
You know, because I've checked me.
I'm showing up so much better.
That is so friggin' important.
And that's every day for me.
This is amazing. Um This is awesome.
Is there before I ask you my my kind of
I have one burning question. Before I ask you my burning question, is there anything else in the planning?
How to make it
Kick ass defining twenty twenty five. Is there anything else we miss before we do that, uh do that, or were those the big ones? I think at like a high level.
Trying to get people to rethink.
How they approach the new year.
I think that
You know
Just get started on those things. I mean you might not have
It all laid out. I don't have it all laid out yet.
But put the stuff you want to do down first.
On a calendar.
Or wherever you want to put it.
And build
A year that you're super proud of.
Because
Let me let me just say this, Sean.
We don't get a lot of ears.
We don't get a lot of years.
And we don't know how many years we're gonna get.
So shame on you if you waste twenty twenty five.
Because you wanna like, oh, I'll just do it next the following year. Like
Time doesn't work like that.
You don't have the luxury of like eh, I'll
The you don't dictate the pace.
Sometimes the pace dictates
You.
And circumstances
Change. And like
You know
Everyone thinks like
I guarantee you
Everybody here knows they're gonna die that's listening to this.
But I guarantee
Less than one percent of our listeners have their graveyard plot picked out.
Because they don't think they're gonna die any time soon.
They don't think that like your life could change like that.
My life's been turned upside down.
I have people that my friends are getting diagnosed with shit.
You know, like it changes, man.
You can go outside and someone could be texting and
He getting smacked.
It just it can go like that. You don't know.
So
You know.
I'm fifty six years old.
The average American lives to be seventy eight.
I don't know. I'm not really good at math.
But that's twenty two years, if I'm average.
And
You know.
I was on the lake this summer, I didn't see a lot of seventy eight year old guys wait boarding.
Like the the years that you have to do an ultraman.
What do they say?
Um, I was just listening to something. They said what, sixty three is the shelf life of like
healthy years or something, you know?
Like it's insane.
So you it's also insane that you plan these you like Well I'll get to it when I'm older.
But then when you're older it's like I don't wanna fucking do that. You know what I mean? Like
Uh you know, I've always criticized actually Warren Buffett where he talks about like delayed gratification and things like this, and I'm like, dude you
You've been the man for years. Like you
Enjoy it. Enjoy that shit now. Like sometimes patience is actually time rich, man. You don't have to be rich to be time rich.
That book that went kinda viral this uh this year or last year, uh Die With Zero.
talks about some of these principles, but he has a great story about one of them that
He's talking about when he was in his twenties and he was on his career ladder climb and he was at some investment bank and
His buddy who we worked with them, they're kind of both twenty three years old or whatever, was like, Hey, dude, what if we just go to Europe backpacking for like, you know, six weeks?
He's like, How are you gonna get six weeks off? He's like
I'm not, I gotta quit.
And like I hope I'll be able to get the job when I come back, but like I'm gonna do this trip.
And he was like, Dude, you're crazy that's like irresponsible. I'm gonna do the responsible thing. And he didn't do that.
And he's he told himself he would do it, you know, maybe next year or the year after that. Maybe he some some reason he'd be able to do it in the future.
So you know.
He's like as soon as he sh came back after six weeks, he didn't have the job back, but he m he met up with the guy. He's like
From the glow on this dude's face, I realized then I made a mistake.
He talks about how when he was thirty three then, ten years later
He finally like took a career break.
He's like,
It's not so cool sleeping in a hostel when you're thirty three.
Um you know it it's a different he's like I learned that it
Some things you can't even just it's not even just doing'em later is worse. He's like
It's just not the same thing. Like that's a twenty three year old trip. I didn't do it when I was twenty three. I did it when I was thirty three or thirty four. And
I had to have a whole different experience. There was no going back to that.
I think it's really important to say yes to adventure.
And um it's never the right time.
You know, like it's never gonna be like oh I have eight days that are clean.
You have to make it. You have to create that.
You know, and I think that's a really important message, like
It's never the right time. You're always gonna I'm gonna miss the basketball game.
You know, there there's always a sacrifice.
But
If you don't do it, you just y you know, you have regret. You just regret it. You just don't get it back.
Well, you said yes to an adventure. You're coming to our basketball camp with Mr Beast, so we'll be seeing you in January for one of those.
Jesse, thanks for coming on. And if you're listening to this, you made it to the end, you're fired up like I am.
We're giving away a few thousand dollars of these calendars, so go to
Jesse, what's the site where people buy the calendar?
I have the code here, but
It's just Jesse Itzler dot com. I think you can get it on my on my website.
So go to JesseEs.com and then use the code WIN
twenty twenty five.
So win two zero two five.
First hundred people that go through go there from this podcast will will get a free big ass calendar. But if you didn't, just buy the th thing and start planning your year. Uh if you're not convinced at this point,
Something's wrong with you.
I had so much fun on the first go round.
You know, Sam gave me a little put me put me under the uh the microscope a little bit. I loved it. I love this his job and I get it.
And um you guys are awesome, man. Like I always get
A lot of DMs about
our our first episode. So
Um to get an invitation back.
was meant a lot to me, man. So
So I you'll get a handwritten letter from me.
I think people don't realize because I mean we host a lot of these and I think um
People forget this, but like
I saw Sean writing. Like I
Like take notes.
Uh just
These are my golden nuggets from this episode. These are you know, my pen dive halfway through.
We appreciate you doing this. Thank you very much.
Until round three, Jesse, thank you.
Thank you.
I feel like I can rule the world, I know I could be what I want to
I'm putting my law in it like my day song On the road less travel never looking back